5 Companies That Encourage Their Employees to Side Hustle

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Most companies want their employees to focus 100% of their attention on their assigned projects and tasks. It makes sense, right? Do the job you’re getting paid to do, and don’t ask questions.

In fact, when I got hired right out of college, my company had a weird habit of transplanting new hires across the country. Why they would pay to relocate people so they could, in some cases, just trade places with each other was confusing to me.

The way it was explained to me was that if they move you across the country away from your existing network of friends and family, you’ll be more focused on your work and the company.

In some ways, it worked. When I moved from Seattle to Virginia, I really didn’t have many friends outside of the office; and it was the same story for many of my younger co-workers.

But rather than pour myself into my job, I poured myself into my side hustle.

One recent trend, especially among technology companies, is to encourage creativity and innovation from within.

For instance, Facebook has their famous “hackathons,” Google has their famous 20% time, and 3M allows workers to spend 15% of their time on internal entrepreneurial pursuits. Word on the street is that’s where the Post-It Note comes from.

Naturally these “intrapreneurial” initiatives are self-serving for the companies. Many of Google’s most profitable products, including Gmail and AdSense, originated from giving employees the freedom and the mandate to dream up something new.

Update: Google’s 20% time may no longer be in effect.

But what about companies that encourage true entrepreneurship among their employees? That is a little more rare, since it might result in less focus at work and potentially higher turnover. As an employer, would you want your workers to be side hustling?

1. Infusionsoft

Earlier this month I was invited to ICON15, an annual conference in Phoenix hosted by Infusionsoft.

I thought it was a little weird they wanted me to come (and pay for my travel expenses as a member of the “press”), since I’m not an Infusionsoft customer and most side hustlers aren’t ready for the investment and functionality that their software comes with.

Still, I was flattered by the offer and wanted to see what it was all about.

It turns out that Infusionsoft is one of the rare companies that encourages its employees to start a business on the side. Since their software is dedicated to serve small businesses, they give every one of their workers a license for free and invite them to use it however they like.

The theory is they’ll be more in tune with what customers want and need if they are users of the software themselves.

infusionsoft stages of small business

I asked Greg Head, Infusionsoft’s Chief Marketing Officer, if he was worried about employee turnover or even lack of dedication if everyone had their own side hustle going on.

He replied with a variation on the classic: “Instead of worrying about what happens if you train your team and they leave, think about what happens if you don’t and they stay.”

Greg also mentioned he was working on a book project of his own as his side hustle. Cheers to authors!

Curious, I began looking for other companies that openly invites employees to start businesses on the side. Here a few more I found.

2. Hubspot

The Boston-based marketing and analytics software company encourages workers to side hustle, either on Hubspot-related projects or something entirely separate.

Even though co-founder Brian Halligan admits that most of these projects fail, having a culture that’s open about entrepreneurship promotes an exciting startup-like DNA within the company, even as they grow.

I connected with one Hubspot entrepreneur who built a cool charcuterie business in her spare time!

3. Basecamp (formerly 37Signals)

Basecamp actually gives out company credit cards to help pay for the outside interests for employees. They only catch is you have to share what you’ve learned with everyone else, which both encourages responsibility and the pursuit of interesting skills and pursuits.

They also experimented with a 4 day work week to help employees pursue outside interests and side hustles.

4. MRY

MRY, a New York-based technology and creative agency, pushes their employees to launch their own products and pursue their individual dreams.

For instance, Brandon Evans launched CrowdTap, a marketing software company, while still at MRY. This side hustle scored more than $10 million in funding, and eventually spun off into its own company, which now has 50+ employees and $8 million in annual revenues.

MRY employees are asked to create an honest “dream resume” — even if their dreams don’t have anything to do with their current roles.

5. Adobe

Adobe’s KickStart Innovation Workshop starts with employees receiving a little red box.

Inside they’ll find a pre-paid credit card and a step-by-step process to brainstorm an innovative new concept and bring it to life. They’re instructed to use the money to validate their concept with real customers.

Your Turn

These innovative companies have found that by fostering the inherent entrepreneurship among their employees, they can generate more winning ideas and better serve their own customers.

Does your company encourage side hustling?

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Nick Loper

About the Author

Nick Loper is a side hustle expert who loves helping people earn more money and start businesses they care about. He hosts the award-winning Side Hustle Show, where he's interviewed over 500 successful entrepreneurs, and is the bestselling author of Buy Buttons, The Side Hustle, and $1,000 100 Ways.

His work has been featured in The New York Times, Entrepreneur, Forbes, TIME, Newsweek, Business Insider, MSN, Yahoo Finance, The Los Angeles Times, The San Francisco Chronicle, The Financial Times, Bankrate, Hubspot, Ahrefs, Shopify, Investopedia, VICE, Vox, Mashable, ChooseFI, Bigger Pockets, The Penny Hoarder, GoBankingRates, and more.

2 thoughts on “5 Companies That Encourage Their Employees to Side Hustle”

  1. Hey Nick, great stuff as always. I just wanted to add one to the list, and I know from personal experience: Shopify.

    They actually found me through my blog and offered me a position as a content marketer. Before taking it, I wanted to ensure I had the freedom to pursue side-hustles. They said “no problem” and explained to me that most people working at Shopify have side-hustles like online stores. Most of the people I work with are entrepreneurs and were before they got hired.

    That’s the kind of thing more companies should encourage and support.


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